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(1,3-Dioxan-2-ylethyl)magnesium bromide solution

0.5 M in THF

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Synonym(s):
1,3-Dioxane - 2-ethyl- magnesium complex, [2-(1,3-Dioxan-2-yl)ethyl]magnesium bromide
Empirical Formula (Hill Notation):
C6H11BrMgO2
CAS Number:
Molecular Weight:
219.36
MDL number:
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

Quality Level

concentration

0.5 M in THF

bp

65 °C

density

0.951 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Br[Mg]CCC1OCCCO1

InChI

1S/C6H11O2.BrH.Mg/c1-2-6-7-4-3-5-8-6;;/h6H,1-5H2;1H;/q;;+1/p-1

InChI key

JYNXRXBIEHSSLR-UHFFFAOYSA-M

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This Item
429007472611442585
density

0.951 g/mL at 25 °C

density

0.941 g/mL at 25 °C

density

0.938 g/mL at 25 °C

density

0.861 g/mL at 25 °C

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

concentration

0.5 M in THF

concentration

0.5 M in THF

concentration

0.5 M in diethyl ether

bp

65 °C

bp

65-67 °C

bp

65-67 °C

bp

34.6 °C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

Application

(1,3-Dioxan-2-ylethyl)magnesium bromide can be used:
  • In a Grignard addition-acylation method for the preparation of enamides.
  • To prepare trisubstituted allenes by reacting with propargylic ammonium salts.
  • In one of the key synthetic steps for the synthesis of febrifugine based antimalarial drugs.

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

pictograms

Exclamation markHealth hazard

signalword

Warning

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - STOT SE 3

target_organs

Respiratory system

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

No data available

flash_point_c

No data available


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Fraser F Fleming et al.
Organic letters, 8(21), 4903-4906 (2006-10-06)
[reaction: see text] Sequential addition of three different Grignard reagents and pivaloyl chloride to 3-oxo-1-cyclohexene-1-carbonitrile installs four new bonds to generate a diverse array of cyclic enamides. Remarkably, formation of the C-magnesiated nitrile intermediate is followed by preferential acylation by
Copper-catalysed cross-coupling of alkyl Grignard reagents and propargylic ammonium salts: stereospecific synthesis of allenes
Guisan-Ceinos M, et al.
Chemical Communications (Cambridge, England), 54(60), 8343-8346 (2018)
Exploration of a new type of antimalarial compounds based on febrifugine.
Kikuchi H, et al.
Journal of Medicinal Chemistry, 49(15), 4698-4706 (2006)
Oxonitriles: A Grignard Addition-Acylation Route to Enamides
Fleming FF, et al.
Organic Letters, 8(21), 4903-4906 (2006)

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